TAILIEUCHUNG - Design, synthesis, and spasmolytic activity of thiophene-based derivatives via Suzuki cross-coupling reaction of 5-bromothiophene-2-carboxylic acid: Their structural and computational studies

In the current research work, a facile synthesis of a series of novel thiophene-based derivatives of 5-bromothiophene-2- carboxylic acid (1) have been synthesized. All analogs (5a-5e, 10a-10f) were obtained from the coupling reaction of 5-bromothiophene2-carboxylic acid (1) and different arylboronic acids with moderate-to-good yields under controlled and optimal conditions. The structures of the newly synthesized compounds were characterized through spectral analysis and their spasmolytic activity, and most of the compounds exhibited potentially good spasmolytic effect. Among the synthesized analogs, compound phenethyl 5-(3,4-dichlorophenyl)thiophene-2-carboxylate (10d) particular showed an excellent spasmolytic effect with an EC50 value of . | Turkish Journal of Chemistry Turk J Chem 2020 44 1410-1422 http chem TÜBİTAK Research Article doi kim-1911-51 Design synthesis and spasmolytic activity of thiophene-based derivatives via Suzuki cross-coupling reaction of 5-bromothiophene-2-carboxylic acid their structural and computational studies 1 2 1 1 Nasir RASOOL Hafiz Mansoor IKRAM Ammara RASHID Nazia AFZAL 3 2 4 5 Muhammad Ali HASHMI Muhammad Naeem KHAN Ayesha KHAN Imran IMRAN 5 6 7 Hafiz Muhammad Abdur RAHMAN Syed Adnan Ali SHAH 1 Department of Chemistry Government College University Faisalabad Faisalabad Pakistan 2 Department of Chemistry University of Sahiwal Sahiwal Pakistan 3 Department of Chemistry University of Education Attock Pakistan 4 School of Chemical and Physical Sciences Victoria University of Wellington Wellington New Zealand 5 Department of Pharmacology Faculty of Pharmacy Bahauddin Zakariya University Multan Pakistan 6 Faculty of Pharmacy Universiti Teknologi MARA Cawangan Selangor Bandar Puncak Alam Selangor Malaysia 7 Atta-ur-Rahman Institute for Natural Products Discovery AuRIns Universiti Teknologi MARA Cawangan Selangor Bandar PuncakAlam Selangor Malaysia Received Accepted Published Online Final Version Abstract In the current research work a facile synthesis of a series of novel thiophene-based derivatives of 5-bromothiophene-2- carboxylic acid 1 have been synthesized. All analogs 5a-5e 10a-10f were obtained from the coupling reaction of 5-bromothiophene- 2-carboxylic acid 1 and different arylboronic acids with moderate-to-good yields under controlled and optimal conditions. The structures of the newly synthesized compounds were characterized through spectral analysis and their spasmolytic activity and most of the compounds exhibited potentially good spasmolytic effect. Among the synthesized analogs compound phenethyl 5- 3 4-dichlorophenyl thiophene-2-carboxylate 10d particular showed an excellent spasmolytic effect .

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